Multiple aggregates from multiple polymorphs: structural and mechanistic insight into organic dye aggregates

Hogan, David T.; Sutherland, Todd C.

doi:10.1039/d2nr03211b

Cited by 2 publications

(3 citation statements)

References 108 publications

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“…Interestingly, it was during the cultivation processes of single crystal for ACIK in various solvents that another kind of platelet-like red single crystals, namely, ACIK-N, was obtained by the slow evaporation from a propanol/chloroform mixture solution (Figure B). ACIK-N displayed NIR emission centered at 687 nm (Φ f = 7.6%), which was spectroscopically matched to the aggregates formed in an acetone/water mixture solution ( f w = 90%) probably owing to their similar aggregation form (Figure C) . The difference of emission maxima between ACIK-Y and ACIK-N was 102 nm, which was relatively large considering they were all constructed from the identical molecule.…”

Section: Resultsmentioning

confidence: 99%

“…ACIK-N displayed NIR emission centered at 687 nm (Φ f = 7.6%), which was spectroscopically matched to the aggregates formed in an acetone/water mixture solution (f w = 90%) probably owing to their similar aggregation form (Figure 2C). 42 The difference of emission maxima between ACIK-Y and ACIK-N was 102 nm, which was relatively large considering they were all constructed from the identical molecule. Impressively, the emission of ACIK-Y was even 20 nm-blue-shifted with respect to that of CIK (λ em = 605 nm), indicating a great potential of aggregation engineering in regulating the optical properties of solid fluorescent materials.…”

Section: Molecular Design and Synthesismentioning

confidence: 99%

“…Moreover, the comparable emission of ACIK dots and ACIK-N (683 nm versus 687 nm) manifested their similar aggregation form in terms of relatively planar molecular conformation and infinite π−π stacking, where the strong push−pull dipolar character as well as the extended π-conjugation were expected to endow ACIK dots with interesting two-photon absorption (2PA) properties. 5,42 For the two-photon excitation process, a fluorophore simultaneously absorbed two photons and was pumped to the excited state, which further underwent a radiative decay pathway to release a photon (Figure 8D). Upon the excitation of a 1040 nm fs laser, the fluorescence spectrum of ACIK dots was recorded in Figure 8E.…”

Section: Mechanochromic Processesmentioning

confidence: 99%

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Molecular and Aggregate Synergistic Engineering of Aggregation-Induced Emission Luminogens to Manipulate Optical/Electronic Properties for Efficient and Diversified Functions

Zheng

Yang

et al. 2023

ACS Nano

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The optical/electronic properties of organic luminescent materials can be regulated by molecular structure modification, which not only requires sophisticated and timeconsuming synthesis but also is unable to accurately afford the optical properties of materials in the aggregate state. Herein, a facile strategy of molecular and aggregate synergistic engineering is proposed to manipulate the optical/electronic properties of a luminogen, ACIK, in the solid state for efficient and diversified functions. ACIK is facilely synthesized and exhibits three polymorphic states (ACIK-Y, ACIK-R, and ACIK-N) with a large emission difference of 102 nm from yellow to nearinfrared (NIR). Their structure−property relationships were investigated by crystallographic analyses and computational studies. ACIK-Y, with the most twisted structure, exhibits an intriguing color-tuned fluorescence between yellow and NIR in the solid state in response to multiple stimuli. Shuttle-like ACIK-R microcrystals exhibit an optical waveguide property with a low optical loss coefficient of 19 dB mm −1 . ACIK dots display bright NIR-I emission, large Stokes shift, and strong NIR-II twophoton absorption. ACIK dots show specific lipid droplets-targeting capability and can be successfully applied for two-photon fluorescence imaging of mouse brain vasculature with deep penetration and high spatial resolution. This study will inspire more insights in developing advanced optical/electronic materials based on a single chromophore for practical applications.

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Section: Resultsmentioning

confidence: 99%

Section: Molecular Design and Synthesismentioning

confidence: 99%

Section: Mechanochromic Processesmentioning

confidence: 99%

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Molecular and Aggregate Synergistic Engineering of Aggregation-Induced Emission Luminogens to Manipulate Optical/Electronic Properties for Efficient and Diversified Functions

Zheng

Yang

et al. 2023

ACS Nano

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Organoboron Polymorphs with Different Molecular Packing Modes for Optical Waveguides

Zhao,

et al. 2024

Chemistry A European J

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Organoboron compounds offer a new strategy to design optoelectronic materials with high fluorescence efficiency. In this paper, the organoboron compound B‐BNBP with double B←N bridged bipyridine bearing four fluorine atoms as core unit is facilely synthesized and exhibits a narrowband emission spectrum and a high photoluminescence quantum yield (PLQY) of 86.53% in solution. Its polymorphic crystals were controllable prepared by different solution self‐assembly methods. Two microcrystals possess different molecular packing modes, one‐dimensional microstrips (1D‐MSs) for H‐aggregation and two‐dimensional microdisks (2D‐MDs) for J‐aggregation, owing to abundant intermolecular interactions of four fluorine atoms sticking out conjugated plane. Their structure‐property relationships were investigated by crystallographic analysis and theoretical calculation. Strong emission spectra with the full width at half maximum (FWHM) of less than 30 nm can also be observed in thin film and 2D‐MDs. 1D‐MSs possess thermally activated delayed fluorescence (TADF) property and exhibit superior optical waveguide performance with an optical loss of 0.061 dB/μm. This work enriches the diversity of polymorphic microcrystals and further reveals the structure‐property relationship in organoboron micro/nano‐crystals.

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Multiple aggregates from multiple polymorphs: structural and mechanistic insight into organic dye aggregates

Abstract: This case study provides evidence for the appearance of multiple aggregation forms of a single organic dye, arising from its packing polymorphs in the solid state. Each aggregate can be...

Cited by 2 publications

References 108 publications

Molecular and Aggregate Synergistic Engineering of Aggregation-Induced Emission Luminogens to Manipulate Optical/Electronic Properties for Efficient and Diversified Functions

Molecular and Aggregate Synergistic Engineering of Aggregation-Induced Emission Luminogens to Manipulate Optical/Electronic Properties for Efficient and Diversified Functions

Organoboron Polymorphs with Different Molecular Packing Modes for Optical Waveguides

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